My boss is a complete moron and a raving lunatic all rolled into one twitchy, befuddled package. I was designing a new part and he wanted to review it so I sent him some CAD drawings. And even though he has no clue what it is I do, how I do it, or in fact any understanding of the requirements for this design, he's the boss so he gets to "suggest" (order) changes.
And since he has this new, very VERY expensive laptop we get to meet in his office to look over the design. Or in other words he wants to impress me with his new toy. Which he has no clue how to use, and got totally hosed when he bought, but he figures he paid a ton of $ for it so it must be the best.
Within two minutes of opening the drawings it's obvious he has no idea how to use the CAD program so he whips out a marker and, wait for it, DRAWS ON THE SCREEN!. I'm dumbfounded. My shock must have been obvious because he said, "Oh, don't worry, it's a dry erase marker." "Sir, I don't think Sharpies come in dry erase form." The look on his face when he realized he'd just ruined a computer that literally cost more then my car was freakin' priceless.